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Erdosteine

Erdosteine

Synopsis, Chemistry

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Also known as: 84611-23-4, Rv 144, Erdosteine [inn], Mucotec, 105426-14-0, Rv-144

Molecular Formula

C₈H₁₁NO₄S₂

Molecular Weight

249.3 g/mol

InChI Key

QGFORSXNKQLDNO-UHFFFAOYSA-N

FDA UNII

76J0853EKA

Erdosteine is a homocysteine-derived thiol derivative with mucolytic and free radical scavenging properties. Erdosteine and its metabolites modulate mucus production and viscosity, by which facilitating mucociliary transport and improving expectoration. This agent also suppresses the chemical-induced cough reflex as well as protects lung tissues from damages caused by cigarette smoking mediated through free radicals scavenging.

1 2D Structure

Erdosteine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-[2-oxo-2-[(2-oxothiolan-3-yl)amino]ethyl]sulfanylacetic acid

2.1.2 InChI

InChI=1S/C8H11NO4S2/c10-6(3-14-4-7(11)12)9-5-1-2-15-8(5)13/h5H,1-4H2,(H,9,10)(H,11,12)

2.1.3 InChI Key

QGFORSXNKQLDNO-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1CSC(=O)C1NC(=O)CSCC(=O)O

2.2 Other Identifiers

2.2.1 UNII

76J0853EKA

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (+-)-((((tetrahydro-2-oxo-3-thienyl)carbamoyl)methyl)thio)acetic Acid

2. Dostein

3. Edirel

4. Esteclin

5. Rv 144

6. Rv-144

7. S-(2-(n-3-(2-oxo-tetrahydrothienyl)acetamido))thioglycolic Acid

8. Vectrine

2.3.2 Depositor-Supplied Synonyms

1. 84611-23-4

2. Rv 144

3. Erdosteine [inn]

4. Mucotec

5. 105426-14-0

6. Rv-144

7. 2-[2-oxo-2-[(2-oxothiolan-3-yl)amino]ethyl]sulfanylacetic Acid

8. 2-((2-oxo-2-((2-oxotetrahydrothiophen-3-yl)amino)ethyl)thio)acetic Acid

9. 76j0853eka

10. Erdosteine (inn)

11. Kw-9144

12. Ncgc00185774-01

13. 2-({[(2-oxothiolan-3-yl)carbamoyl]methyl}sulfanyl)acetic Acid

14. Acetic Acid, [[2-oxo-2-[(tetrahydro-2-oxo-3-thienyl)amino]ethyl]thio]-

15. Dsstox_cid_28661

16. Dsstox_rid_82931

17. Dsstox_gsid_48735

18. Erdosteinum [latin]

19. Dithiosteine

20. Erdosteinum

21. Vectrine

22. Edirel

23. ({2-oxo-2-[(2-oxotetrahydro-3-thienyl)amino]ethyl}sulfanyl)acetic Acid

24. Acetic Acid, ((2-oxo-2-((tetrahydro-2-oxo-3-thienyl)amino)ethyl)thio)-

25. Cas-84611-23-4

26. Secresolv

27. Erdosteine [inn:ban]

28. Pv 144

29. Erdostiene

30. Erdotin

31. Unii-76j0853eka

32. 2-(2-oxo-2-(2-oxotetrahydrothiophen-3-ylamino)ethylthio)acetic Acid

33. Erdosteine,(s)

34. Mucotec (tn)

35. Erdosteine [mi]

36. Dl-s-(2-(n-3-(2-oxotetrahydrotheinyl)acetamido))thioglycolic Acid

37. ((2-oxo-2-((tetrahydro-2-oxo-3-thienyl)amino)ethyl)thio)acetic Acid

38. (+-)-((((tetrahydro-2-oxo-3-thienyl)carbamoyl)methyl)thio)acetic Acid

39. Acide ((2-oxo-3-tetrahydrothienylcarbamoyl)-methylthio)acetique [french]

40. Erdosteine [mart.]

41. Erdosteine [who-dd]

42. Schembl21721

43. Mls006010056

44. Chembl1697744

45. Dtxsid8048735

46. Erdosteine, >=98% (hplc)

47. Chebi:135014

48. Hms3264c11

49. Hms3655i14

50. Acide ((2-oxo-3-tetrahydrothienylcarbamoyl)-methylthio)acetique

51. Hy-b0289

52. Tox21_113176

53. Mfcd00867664

54. S1825

55. Stl452949

56. Akos015888361

57. Tox21_113176_1

58. Ac-5278

59. Ccg-213836

60. Db05057

61. Ks-1352

62. Ncgc00185774-02

63. Ncgc00185774-09

64. Smr002529560

65. E1026

66. Ft-0625684

67. Ft-0630929

68. Sw220302-1

69. D07383

70. T72990

71. Ab01274804-01

72. Ab01274804_02

73. Ab01274804_03

74. 611e234

75. A840878

76. Sr-01000944253

77. Q3731252

78. Sr-01000944253-1

79. N-(tetrahydro-2-oxo-3-thienyl)-3-thiapentanedioic Acid Monoamide

80. ({2-oxo-2-[(2-oxotetrahydrothiophen-3-yl)amino]ethyl}sulfanyl)acetic Acid

81. (+/-)-((((tetrahydro-2-oxo-3-thienyl)carbamoyl)methyl)thio)acetic Acid

82. 2-[2-oxo-2-[(2-oxotetrahydrothiophen-3-yl)amino]ethyl]sulfanylacetic Acid;erdosteine

83. Erdosteine; [[2-oxo-2-[(tetrahydro-2-oxo-3-thienyl)amino]ethyl]thio]acetic Acid

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₈H₁₁NO₄S₂
Molecular Weight	249.3 g/mol
XLogP3	-0.1
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	5
Exact Mass	249.01295018 g/mol
Monoisotopic Mass	249.01295018 g/mol
Topological Polar Surface Area	134 Å²
Heavy Atom Count	15
Formal Charge	0
Complexity	282
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Fro the treatment of chronic bronchitis in adults.

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Expectorants

Agents that increase mucous excretion. Mucolytic agents, that is drugs that liquefy mucous secretions, are also included here. (See all compounds classified as Expectorants.)

5.2 ATC Code

R05CB15

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

R - Respiratory system

R05 - Cough and cold preparations

R05C - Expectorants, excl. combinations with cough suppressants

R05CB - Mucolytics

R05CB15 - Erdosteine

5.3 Mechanism of Action

Erdosteine, is an orally administered mucolytic agent. It is classified as a thiol derivative and produced for the management of symptoms caused by chronic obstructive bronchitis. Erdosteine contains sulfhydryl groups which are released after hepatic first-pass metabolism in the liver. Its active metabolites (3 in number) exert both mucolytic activity and scavenging activity against free radicals. Erdosteine acts to regulate the production of mucus in the airway and regulates its viscosity while enhancing mucociliary transport. This leads to an increase in expectoration. Erdosteine shows inhibition against the effects of free radicals from cigarette smoke. Clinical studies in patients with chronic obstructive lung disease (COPD) have shown that this drug is generally safe and well tolerated. Erdosteine 300mg twice daily reduced cough (both frequency and severity) and sputum viscosity more quickly and more effectively than placebo and reduced the adhesivity of sputum more effectively than ambroxol 30mg twice daily. Co-administration of erdosteine and amoxicillin in patients with acute infective exacerbation of chronic bronchitis resulted in higher concentrations of the antibiotic in the sputum, leading to earlier and more pronounced amelioration of clinical symptoms compared with placebo. Erdosteine is associated with a low incidence of adverse events, most of which are gastrointestinal and generally mild.